Methanol → Methyl 4-bromo-3-(trifluoromethyl)benzoate

Thionyl chloride (16.2 mL, 223 mmol) was added dropwise over 15 min into a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (Acceledev 000625, 15.0 g, 55.8 mmol) in MeOH (300 mL). The resulting mixture was stirred at RT for 12 hours. The reaction mixture was concentrated under reduced pressure. The residue was taken up with EtOAc (500 mL) and washed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL). The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure affording the title compound as an orange solid (14.8 g, 94%). HPLC (Method A), Rt 4.7 min (Purity: 99.0%). 1H NMR (DMSO-d6, 300 MHz) δ 8.26 (m, 1H), 8.14 (m, 2H), 3.93 (s, 3H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. washwashed with a saturated aqueous solution of NaHCO3 (200 mL), water (200 mL) and brine (200 mL)
3. dry with materialThe organic layer was dried (MgSO4)
4. customthe solvent was removed under reduced pressure

ORD record

ord-13f2d9f15c8e4173bd9b2c6322f4883c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791142B2